Total Syntheses of Optically Active 19-Norsteroids. (+)-Estr-4-ene-3,17-dione and (+)-13β-Ethylgon-4-ene-3,17-dione

Journal of Organic Chemistry

Volumn 40, Issue 6, 1975, Pages 675-681

  Micheli, Robert A ^a   Hajos, Zoltan G ^a   Cohen, Noal ^a   Parrish, David R ^a   Portland, Louis A ^a   Sciamanna, Werner ^a   Scott, Melinda A ^a   Wehrli, Pius A ^a  

^a HOFFMANN LA ROCHE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

13BETA ETHYLGON 4 ENE 3,17 DIONE; ESTR 4 EN 3,17 DIONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; POLARIMETRY; THEORETICAL STUDY; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY;

ESTRENES; GONANES; KETOSTEROIDS; METHODS; NORSTEROIDS; OPTICAL ROTATION;

EID: 0016691895     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00894a003     Document Type: Article

References (27)

1. Z. G. Hajos and D. R. Parrish, J. Org. Chem., 38, 3244 (1973).
2. G. Saucy and N. Cohen, in “MTP International Review of Science,” Series One, Vol. 8, Steroids, W. F. Johns, Ed., Butterworths, London, England, 1973, p 1.
3. R. Pappo in “The Chemistry and Biochemistry of Steroids,” Vol. 3, No. 1, N. Kharasch, Ed., Intra-Science Research Foundation, Santa Monica, Calif., 1969, p 123.
4. A. L. Wilds and N. A. Nelson, J. Amer. Chem. Soc., 75, 5366 (1953).
5. U. S. Patent No. 3395080 (American Home Products); Chem. Abstr., 70, P 189, 10b, (1969).
6. Z. G. Hajos and D. R. Parrish, J. Org. Chem., 39, 1615 (1974).
7. Z. G. Hajos and D. R. Parrish, J. Org. Chem., 39, 1612 (1974).
8. J. B. Gardner, B. A. Anderson, and E. P. Oliveto, J. Org. Chem., 34, 107 (1969).
9. Z. G. Hajos, D. R. Parrish, and E. P. Oliveto, Tetrahedron, 24, 2039 (1968).
10. H. C. Beyerman and G. L. Heiszwolf, Recl. Trav. Chlm. Pays-Bas, 84, 203(1965).
11. Z. G. Hajos, R. A. Micheli, D. R. Parrish, and E. P. Oliveto, J. Org. Chem., 32, 3008 (1967).
12. Z. G. Hajos and D. R. Parrish, J. Org. Chem., 38, 3239 (1973).
13. H. L. Finkbeiner and M. Stiles, J. Org. Chem., 28, 216 (1963).
14. H. L. Finkbeiner and M. Stiles, J. Amer. Chem. Soc., 85, 616 (1963).
15. M. Stiles, J. Amer. Chem. Soc., 81, 2598 (1959).
16. S. Julla and C. Huynh, C. R. Acad. Sci., Ser. C, 270, 1517 (1970).
17. C. Huynh and S. Julla, Bull. Soc. Chim. Fr., 1794 (1972).
18. J. W. Scott, P. Buchschacher, L. Labler, W. Meier, and A. Fürst, Helv. Chim. Acta, 57, 1217 (1974).
19. E. Roman, A. J. Frey, P. A. Stadler, and A. Eschenmoser, Helv. Chim. Acta, 40, 1900 (1957).
20. W. Ried and W. Kunstman, Chem. Ber., 100, 605 (1967).
21. L. F. Fieser and M. Fieser, “Steroids,” Reinhold, New York, N.Y., 1959, p 588.
22. H. Smith, G. A. Hughes, G. H. Douglas, G. R. Wendt, G. C. Buzby, Jr., R. A. Edgren, J. Fisher, T. Foell, B. Gadsby, D. Hartley, D. Herbst, A. B. A. Jansen, K. Ledlg, B. J. McLaughlin, J. McMenamin, T. W. Pattison, P. C. Phillips, R. Rees, J. Siddall, J. Siuda, L. L. Smith, J. Tokollcs, and D. H. P. Watson, J. Chem. Soc., 4472 (1964).
23. K. Bowden, I. M. Hellbron, E. R. H. Jones, and B. C. L. Weedon, J. Chem. Soc., 39 (1946).
24. A. J. Birch, J. A. K. Quartey, and H. Smith, J. Chem. Soc., 1768 (1952).
25. J. D. Cocker and T. G. Halsall, J. Chem. Soc., 3441 (1957).
26. C. B. C. Boyce and J. S. Whitehurst, J. Chem. Soc., 2680 (1960).
27. T. A. Spencer, H. S. Neel, D. C. Ward, and K. L. Williamson, J. Org. Chem., 31, 434 (1966).